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681-84-5

Basic Information
CAS No.: 681-84-5
Name: Tetramethyl orthosilicate
Article Data: 121
Cas Database
Molecular Structure:
Molecular Structure of 681-84-5 (Tetramethyl orthosilicate)
Formula: C4H12O4Si
Molecular Weight: 152.222
Synonyms: Methylsilicate ((MeO)4Si) (6CI);Dynasil M;Methyl Silicate 28;Methyl Silicate 39;Methyl orthosilicate;Methyl silicate((CH3)4SiO4);Silane, tetramethoxy-;Siliconmethoxide (Si(OMe)4);Silicon tetramethoxide;Siluplex;Tetramethoxysilane;Tetramethyl silicate;Methyl silicate;
EINECS: 211-656-4
Density: 0.977 g/cm3
Melting Point: -4 °C(lit.)
Boiling Point: 121.207 °C at 760 mmHg
Flash Point: 28.889 °C
Solubility: hydrolysis in water
Appearance: Colorless transparent liquid
Hazard Symbols: VeryT+
Risk Codes: 10-26-37/38-41
Safety: 16-26-36/37/39-45-28A
Transport Information: UN 2606 6.1/PG 1
PSA: 36.92000
LogP: 0.00760
Synthetic route
67-56-1

methanol

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With amorphous silicon In hexane at 20℃; Temperature; Solvent; Inert atmosphere; Schlenk technique; Cooling with ice;98%
With nickel(II) sulphate; tetrachlorosilane; trichlorosilane In tetrachloromethane at 55 - 60℃; for 3h; Large scale;96.8%
Stage #1: methanol With iodine; silicon tetrafluoride; aluminium at 37℃; for 2.5h;
Stage #2: at 40℃; for 2.5h; Reflux;
86%
67-56-1

methanol

7783-61-1

silicon tetrafluoride

7439-95-4

magnesium

A

magnesium fluoride

B

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
Stage #1: methanol; magnesium With iodine at 20℃; for 1.5h; Inert atmosphere; Reflux;
Stage #2: silicon tetrafluoride Inert atmosphere;
Stage #3: at 300℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Calcination;
A 98%
B 85%
Stage #1: methanol; magnesium at 20℃; for 3h;
Stage #2: silicon tetrafluoride at 20℃; for 0.5h; Temperature;
7783-61-1

silicon tetrafluoride

A

ammonium hexafluorosilicate

B

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With CH3OH; NH3 In methanol introduction of NH3 into CH3OH in absence of air; introduction of SiF4;; filtration; distn. of the filtrate;;A n/a
B 95%
With methanol; ammonia In methanol introduction of NH3 into CH3OH in absence of air; introduction of SiF4;; filtration; distn. of the filtrate;;A n/a
B 95%
5625-96-7

(morpholinomethyl)hydrosilane

67-56-1

methanol

A

109-02-4

4-methyl-morpholine

B

681-84-5

tetramethylorthosilicate

C

154206-90-3

α-morpholine methyltrimethoxysilane

Conditions
ConditionsYield
In neat (no solvent) at 0 - 5℃; for 5h; Mechanism; Inert atmosphere;A 5.5%
B 5.5%
C 90%
10026-04-7, 53609-55-5

tetrachlorosilane

624-91-9

methyl nitrite

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
SiCl4 and a small excess of methylnitrite in absence of moisture under cooling; slow heating at about 120°C;;80%
10026-04-7, 53609-55-5

tetrachlorosilane

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With methanol In methanol fast addn. of SiCl4 to a small excess of CH3OH (ice bath);; fractional distn.;;80%
With CH3OH SiCl4 and CH3OH in presence of CH3COONa;;80%
With CH3OH In methanol fast addn. of SiCl4 to a small excess of CH3OH (ice bath);; fractional distn.;;80%
67-56-1

methanol

102-71-6

triethanolamine

A

681-84-5

tetramethylorthosilicate

B

2C6H15NO3*F6Si(2-)*2H(1+)

Conditions
ConditionsYield
Stage #1: methanol With Hexafluoropropene oxide at 20℃;
Stage #2: triethanolamine In methanol for 1h;
A n/a
B 71%
67-56-1

methanol

A

681-84-5

tetramethylorthosilicate

B

4371-91-9

hexamethoxydisiloxane

Conditions
ConditionsYield
With copper(l) chloride; silicon at 250℃; under 159611 Torr; for 3h; Temperature; Pressure; Autoclave;A 70%
B n/a
7440-21-3

silicon

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With methanol In neat (no solvent) heating of Si at 1050°C in H2-atm. for 2 h in presence of Cu-oxide, Cu-halide or Cu-nitrate; dropwise addn. of CH3OH at 300°C;;50%
With methanol; copper In neat (no solvent) heating of Cu and Si at 1050°C in H2-atm. for 2 h; dropwise addn. of CH3OH at 300°C;;50%
With CH3OH; copper In neat (no solvent) heating of Cu and Si at 1050°C in H2-atm. for 2 h; dropwise addn. of CH3OH at 300°C;;50%
67-56-1

methanol

29167-65-5

tris(silatranyloxyethyl)amine

681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With hydrogenchloride38%
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Chemistry


IUPAC Name: Tetramethyl silicate 
Empirical Formula: C4H12O4Si
Molecular Weight: 152.2212
Canonical SMILES: CO[Si](OC)(OC)OC
InChI: InChI=1S/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3
InChIKey: LFQCEHFDDXELDD-UHFFFAOYSA-N
EINECS: 211-656-4
Product Categories: Silicate; Organics; Si (Classes of Silicon Compounds); Si-O Compounds; Tetraalkoxysilanes; Crosslinkers; Crosslinking Agents; Orthosilicate 
Appearance: colourless liquid 
Melting point: 4-5 °C
Solubility in water: organic solvents 
storage temp.: Flammables area
Sensitive: Moisture Sensitive 
Index of Refraction: 1.382
Molar Refractivity: 36.27 cm3
Molar Volume: 155.7 cm3
Surface Tension: 19.9 dyne/cm
Density: 0.977 g/cm3
Flash Point: 28.9 °C
Enthalpy of Vaporization: 34.44 kJ/mol
Boiling Point: 121.2 °C at 760 mmHg
Vapour Pressure of Methyl silicate (CAS NO.681-84-5): 17.7 mmHg at 25 °C

Uses

In organic synthesis, Methyl silicate (CAS NO.681-84-5) has been used to convert ketones and aldehydes to the corresponding ketals and acetals, respectively.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral 1gm/kg (1000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse LCLo inhalation 1gm/m3/10M (1000mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

MUSCULOSKELETAL: OTHER CHANGES
National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. MAY1942,
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 2, Pg. 56, 1950.
rabbit LD50 skin 17mL/kg (17mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rabbit LDLo intravenous 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
"Dangerous Properties of Industrial Materials," Sax, N.I., New York, Van Nostrand Reinhold, 1980Vol. 3, Pg. 935, 1968.
rat LCLo inhalation 250ppm/4H (250ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD50 intraperitoneal 100mg/kg (100mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1222, 1986.
rat LDLo oral 700mg/kg (700mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" "Dangerous Properties of Industrial Materials," Sax, N.I., New York, Van Nostrand Reinhold, 1980Vol. 3, Pg. 935, 1968.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by inhalation. Mildly toxic by skin contact. A severe eye irritant. This material can cause extensive necrosis (experimentally), keratoconus, and opaque cornea. It also causes severe human eye injuries, as well as necrosis of corneal cells, which progresses long after exposure has ceased. It is destructive and its effects resist treatment. Permanent blindness is possible from exposure to it. The kidney seems to be most subject to injury regardless of the mode of exposure. Pulmonary edema has also occurred. This material is more toxic than either ethyl silicate or silicic acid, although it has been thought that the injury caused is largely due to the action of the silicic acid. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. Potentially violent reaction with metal hexafluorides (e.g., rhenium, molybdenum, tungsten). When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: VeryT+
Risk Statements: 10-26-37/38-41 
R10:Flammable. 
R26:Very toxic by inhalation. 
R37/38:Irritating to respiratory system and skin. 
R41:Risk of serious damage to the eyes.
Safety Statements: 16-26-36/37/39-45-28A 
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2606 6.1/PG 1
WGK Germany: 3
RTECS: VV9800000
F: 10-21
TSCA: Yes
HazardClass: 6.1
PackingGroup: I

Standards and Recommendations

OSHA PEL: TWA 1 ppm
ACGIH TLV: TWA 1 ppm
DOT Classification:  3; Label: Flammable Liquid, Poison

Specification

 Methyl silicate (CAS NO.681-84-5), its Synonyms are Tetramethoxysilane ; Tetramethyl silicate ; Methyl Silicate 39 ; Methyl orthosilicate ; Silane, tetramethoxy- ; Silicic acid, methyl ester of ortho- ; Silicic acid, tetramethyl ester ; Tetra-methyl orthosilicate .